For at least the past two decades, I’ve been puzzling through personal productivity, trying to figure out systems and approaches and tools and hacks that help me get stuff done. On the one hand, I feel pretty excellent about how that’s worked, as I’ve managed to make a bunch of things in the world. On the other, during those twenty years, I’ve also felt behind and overwhelmed, have procrastinated and mis-prioritized, and consistently fell short of what I actually wanted to accomplish on most days.

Looking back, it’s clear those struggles boil down to two major challenges:

– Not taking on more each day than could even possibly be squeezed into 24 hours.

– Actually doing the most important, but also most difficult, tasks on my to-do list.

So far this year, I’ve been thinking a bunch about the first of those two challenges, which has led me to pare waaaaaay back. I’ve tried to reduce my obligations, whether work or play, to others or to myself, in an effort to align my plans and intentions better with the limits of reality. And though maintaining that more minimal approach requires ongoing work—mostly, regularly weeding my commitments, as old obligation-adding habits die hard—it seems to be going pretty well.

Where I’ve continued to fall short, however, is on the second challenge: completing (or, honestly, even just getting started on) each day’s important but difficult tasks. Sometimes, that’s because other, genuinely urgent tasks crop up. More often, it’s because I end up doing a bunch of easier ‘bullshit work’ tasks instead. (And, at least once or twice a week, it’s because I self-soothe task list overwhelm by deep-diving into some semi-relevant research rabbit hole for hours and hours at a stretch.)

Thinking about the important / difficult task challenge, I’ve come to realize it’s fundamentally a question of keeping my word. In this case, keeping my word to myself. Putting a task on my to-do list is essentially a promise I’m making that I’m going to do that task. Each day I do other stuff instead, I’m breaking those promises, again and again.

Which is why I was recently particularly interested to discover a new exercise from Mark Forster, one of my favorite time management thinkers. His idea, essentially, is to build that kind of self-promising skill, incrementally, with a deliberate practice approach. Here’s how it works:

First, choose a single task (not an entire project, just something finite and concrete, a first step). Define what ‘completion’ means for that task (e.g., finish a first draft of the proposal, make the call, finish reading the chapter). And then do that task to completion.

Your score is now one.

Next, choose two tasks. Do them each to completion, in order. Your score is two.

Now back for three tasks, etc. You’re permitted to do non-discretionary tasks in the middle of each pass—taking on something your boss tells you to do immediately, going to a meeting, addressing a genuine emergency. But you can’t do any discretionary task other than the next task on your list.

If you do, your final score for the round is the last batch you successfully completed (i.e., if you fail partway through a seven-task group, your score is the completed round of six). Start again with a single task, and build up a new score from one.

The aim here isn’t to keep going up forever. Instead, it’s simply to increase over time the size of task group that you’re able to reliably complete.

So far, I’ve only been trying out the approach for a few days. And I still, decisively, suck at it. But I’m loving the approach nonetheless. It’s gamified in a fun and motivating way, while still providing clear, structured, and immediate feedback—exactly what’s required for practice that yields genuine improvement over time.

At this point, I’m not entirely certain that the exercise is sustainable over the long-haul. But, for the moment at least, I’m glad to be doing it, glad to be directly addressing my second big time management challenge. It feels like the best plan I’ve found thus far for building a fundamental productivity keystone skill: knowing I can make myself do something important just by telling myself that I will.

Since the start of the year, I’ve been trying to do less, better. And, in the process, I’ve reinforced a lesson I’d several times previously learned: the relationship between the length of my to-do list and my productivity output is shaped like a bell curve. If I don’t put things on my list, they don’t get done. (I realize that sounds tautological, but I mostly mean that I’m terrible at remembering to bang out even minor tasks in the open stretches of my day, if I don’t have them on a list in front of me.) Conversely, if I put too much on my list, my productivity similarly diminishes. I use the glut of easy tasks to procrastinate around the important ones, or reach general overwhelm and don’t do much of anything useful at all.

So getting a Goldilocks length right on my to-do list each day – not too short, not too long – makes a huge difference.

For projects, that’s meant taking a Kanban-esque approach, and strictly limiting ‘work in progress’ at every level, whether quarterly, monthly, weekly, or daily. And, by and large, that’s worked pretty well.

But a bunch of my time is also spent on more open-ended commitments – regular habits like playing the trumpet, meditating, or working out, as well as semi-regular ones, like occasionally deep-cleaning the kitchen, or making it to a museum, live theater performance, and live music show each month (at least when the world isn’t on lockdown).

For those habits, the best thing I’ve been able to do is to simply downshift their frequency – say, moving monthly ones to quarterly schedules instead – or to drop some of them completely. And, indeed, that’s helped further hone my daily list to a far more manageable length.

Still, not all of those de-prioritizations have sat well with me. While I’ve never been a consistent, daily blogger, I’ve at least previously tried to trend in that direction. But, in my habit purge, I downgraded my intention to posting weekly. And, in short, I missed it.

So, in the last week, I’ve been upshifting or adding back in a few of the habits I regretted excising or downgrading. But I’ve been doing it cautiously, trying hard not to overshoot, lest I again end up on the downhill slope on the far side of my to-do list length curve.

Really, it’s all just a playing out of one of my perpetual core struggles. For better or worse, I’m more a fox than a hedgehog. And though I genuinely believe I would accomplish more in the world were I laser-focused on a single life pursuit, I’m also passionate about a bunch of different things, and it’s exceedingly tough for me to give them up.

Hence, in turn, my tendency to overload my to-do list. So, even as I slowly build it back up, I’m trying to remind myself of my overarching push for 2020, my aim to do less, better. I’m trying to keep in front of me the old French proverb: “Qui chasse deux lièvres n’en prend pas un.” He who chases two hares, catches none.

Like many people these days, I’ve been sleeping poorly, and having all kinds of weird dreams. Part of that, I know from experience, is simply a lack of movement throughout the day. While I’m still exercising, my overall, non-exercise movement has dropped steeply. (For example, my daily step count is down about two-thirds, from a pre-lockdown average of ~15,000 a day, to just ~5,000 now). And, obviously, a lot comes from the huge underlying stress inherent in living through this pandemic. But, beyond those two factors, I also suspect it’s due to lack of a fixed schedule. Of late, my wake-up and bedtimes have drifted all over the place.

Similarly, my productivity has been pretty erratic. Some days, I bang out a huge amount of work, while others I manage to make it to evening having accomplished essentially nothing at all. And here, too, I think the lack of fixed schedule is screwing me up. To state the obvious, if I sit down and start working, I’m much more likely to get things done than if I wander around and scroll through Twitter and space out.

So, starting tomorrow, I’m instituting time-blocking, at least for weekdays. The chunks are still pretty big and open – wake up at 7am, then exercise, shower, and caffeinate.  Kick off a ‘deep work’ block at 9am, focused on my big project for the day. Lunch break at noon, back to smaller tasks at 1pm, then calling it a day at 4pm, and working on personal projects and habits (like practicing trumpet or writing this blog), before cooking dinner at 6pm, and relaxing with Jess for the evening until we hit the hay at 11pm.

Historically, I’m pretty terrible at sticking with this kind of schedule. But, at the moment, I have waaaaay less calendared in the weeks ahead than I would in non-lockdown life, and many fewer external disruptions to derail me throughout the day. And, honestly, even if I don’t really end up sticking with the schedule precisely, I suspect even just pushing in that direction would help a whole lot. But, I guess, time will tell.  ¯\_(ツ)_/¯

My father once told me he’d learned over time that to-do lists are kind of like the tides: sometimes it’s high tide, and sometimes it’s low tide, but he’d always been trying to reach no water, and he’d eventually realized that just wasn’t going to happen.

I’ve been thinking about that of late, whenever I see various ‘things to do during self-isolation’ lists getting emailed around, or people complaining on Twitter about being bored out of their minds.  Because, on my end, even having cleared my schedule of every outside-the-apartment appointment and obligation, I’m still making it to the end of each day feeling totally behind on everything I could and should be doing.

That said, I’ve also been extremely productive.  I just have so much more that I want to get done.  And that doesn’t even include the less urgent and obligated stuff, like catching up on the pile of books I’m hoping to read, or the list of movies I’d like to watch, or just taking some time to stare out the window and reflect on the big picture of life.

Part of the problem, I think, is that I still don’t really have a fixed schedule.  I’m hoping to get that figured out shortly, adding a more formal start and end to my workday, making sure I observe an actual weekend.  Anything that adds some regularity and contour to my self-isolated life.  This whole thing could stretch on for quite a while, and as much as I’d like to come out the other end with a list of accomplishments, I’m even more concerned about getting there with my sanity still intact.

I was in the gym with clients from early this morning, but came back at lunchtime to work the balance of the day at home. Or, at least, that was the plan. Instead, I seem to be an object at rest, unable to overcome the inertia of our couch.

I’m trying; I really am. Even this blog post is an attempt to kick-start things, to get rolling by knocking out some quick, easy to-do list wins.

And, perhaps, that will work, and I can pick up momentum as I go. From past experience I’ve learned that sometimes days like this, despite their slow starts, turn out on balance to be highly productive in the end.

But other times, I just stay stuck, don’t really accomplish much at all. And though, earlier in life, those sort of no-progress, do-nothing days stressed me out, I now increasingly think: sometimes that’s just the kind of day it is. And that’s okay, too.